Henry Starr — The Cherokee Bad Boy
Henry Starr, a name synonymous with daring heists and a life lived on the fringes of the law, carved a notorious path through the American West. His criminal career, spanning from the era of horseback robberies to the dawn of the automobile age, saw him become one of the most prolific bank robbers in American history. Starr’s legacy is a complex tapestry woven with threads of Cherokee heritage, family notoriety, and a relentless pursuit of outlawry.
Early Life and Influences
Born near Fort Gibson in the Indian Territory (present-day Oklahoma) on December 2, 1873, Henry Starr inherited a mixed lineage that would shape his destiny. His father, George "Hop" Starr, was of half-Cherokee descent, while his mother, Mary Scot Starr, boasted Irish ancestry and one-quarter Cherokee blood. While Mary’s family was known for its education and respectability, the Starr side was steeped in a tradition of outlawry.
Henry’s grandfather, Tom Starr, was an outlaw of considerable repute, described by Henry himself as "known far and wide as the Devil’s own. In all matters where law and order were on one side, Tom Starr was on the other." This familial connection to the criminal underworld undoubtedly played a role in shaping young Henry’s worldview.
Further solidifying his connection to outlawry was his uncle, Sam Starr, famously married to Belle Starr, the "Outlaw Queen." Belle was renowned for her association with the notorious Younger Gang and her own exploits throughout Oklahoma. However, Henry held a distinct disdain for Belle, finding her coarse and objectionable. He was quick to clarify that she was only his aunt through marriage, distancing himself from her reputation.
The environment of Starr’s youth further contributed to his trajectory. The northeastern corner of Indian Territory in the late 19th century was a lawless frontier, often dubbed the "Land of the Six-Gun" and the "Robbers’ Roost." The rugged terrain provided ample natural hiding places for outlaws, murderers, and thieves seeking to evade the reach of the law.
A Descent into Crime
In 1886, tragedy struck when Henry’s father passed away, leaving Mary to care for her three children and the family farm. Within months, Mary remarried a man named C.N. Walker, whom Henry deeply resented. Starr believed Walker to be inferior due to his lack of Native American ancestry. Walker’s abusive nature further strained their relationship, leading Henry to leave home shortly after the marriage.
At the age of sixteen, Henry found work on a ranch near Nowata in Indian Territory, marking his first encounter with the law. While driving a wagon to town, he was apprehended by two deputy marshals for "introducing spirits into the territory." Although he pleaded guilty, he maintained his innocence, claiming he had borrowed the wagon unaware of the whiskey concealed within.
Despite this initial brush with the law, Henry returned to Nowata and continued working as a cowboy. However, it wasn’t long before he found himself in trouble again. In December 1891, he was arrested for horse theft. Again, he denied the charge but was incarcerated at Fort Smith, Arkansas. His cousin posted his bail, but Starr chose to flee, becoming a fugitive with a warrant hanging over his head. This decision marked a turning point, solidifying his path towards a life of crime.
The Starr Gang and Early Robberies
Teaming up with Ed Newcome and Jesse Jackson, Henry Starr formed a gang that targeted stores and railroad depots. Their first heist occurred in July 1892, when they relieved the Nowata Depot of $1,700. In November of the same year, they robbed Shufeldts Store at Lenapah, Indian Territory, taking $300, and Carter’s Store in Sequoyah, Indian Territory, making off with $180.
By December 1892, Deputy Marshals Dickey and Wilson were closing in on Henry. Following his trial, the two marshals arrived at Arthur Dodge’s "XU Ranch," eight miles from Nowata, where the Starr Gang was rumored to be meeting. Dodge denied knowing Starr personally but admitted to seeing him ride by the ranch on several occasions. After searching the surrounding countryside without success, the lawmen returned to the Dodge Ranch for dinner the following day. Dodge then informed them that he had spotted Henry while working on the ranch.
Deputy Wilson immediately pursued Henry, leading to a dramatic confrontation on Wolf Creek. Starr and Wilson exchanged gunfire, resulting in Wilson being fatally wounded. Henry escaped, now wanted for murder, further escalating the pursuit by law enforcement.
In January 1893, Starr narrowly avoided capture during a gun battle with Indian Police near Bartlesville, I.T. He then partnered with Frank Cheney, and together they robbed the MKT railroad depot of $180 and Haden’s Store of $390 in Choteau. In February, they targeted the railroad depot and general store in Inola, making off with $220.
Escalation to Bank Robbery
Seemingly emboldened by their success and undeterred by the relentless pursuit of the law, Starr and Cheney escalated their criminal activities by robbing their first bank in Caney, Kansas, on March 28, 1893. They relieved the Caney Valley Bank of $4,900. The brazen nature of the robbery, in which they entered the bank with revolvers drawn and locked the customers and employees in a back room, shocked the community. One Kansas newspaper described it as "one of the boldest and most daring robberies known to border history."
A little over a month later, they robbed their first passenger train at Pryor Creek, netting $6,000.
Undeterred, Henry Starr chose the People’s Bank of Bentonville, Arkansas, for their next robbery. On June 5, 1893, Starr and four partners rode into the small town. However, by this time, Starr’s notoriety had grown, and he was recognized upon entering the town.
As Starr and Kid Wilson entered the bank, an alarm was raised, and gunfire erupted outside. The duo fled the bank while the robbery was still in progress, racing for their horses with a posse in hot pursuit. They counted their loot to find only $11,000, which had to be split between five men.
Capture and Trials
Following the Bentonville robbery, the law relentlessly pursued Starr and his gang. With a $5,000 reward offered for Starr’s capture, the gang decided to split up temporarily. Henry, Kid Wilson, and a female companion boarded a train at Emporia, Kansas, intending to travel to California. They stopped in Colorado Springs to shop and sightsee. On July 3, 1893, they checked into the Spaulding House, registering under false names. However, officers discovered their presence, and Starr was arrested in the restaurant. Wilson was later apprehended in Colorado City. A search of their room revealed $1,460 in cash and approximately $500 in gold.
Starr and Wilson were returned to Fort Smith, Arkansas, on July 13, 1893, to face trial. Starr was charged with thirteen counts of highway robbery and one count of murder. The trial focused on the murder charge, and Starr was found guilty by Judge Isaac Parker and sentenced to hang. However, his lawyers appealed the decision, and the U.S. Supreme Court overturned Parker’s ruling and granted Starr a new trial. He was found guilty at the second trial and again sentenced to hang, but his lawyers again appealed, securing yet another trial.
At the third trial, Henry Starr pleaded guilty to manslaughter and was sentenced to a total of 15 years in prison. On January 15, 1898, he was transported to the federal prison in Columbus, Ohio.
Imprisonment and Pardon
While awaiting trial at Fort Smith, Arkansas, Starr witnessed a dramatic jailbreak attempt by fellow prisoner Crawford Goldsby, alias Cherokee Bill. During the ensuing gun battle between Bill and the prison guards, one of the guards was killed. Henry, an acquaintance of Cherokee Bill, offered to disarm him if the guards promised not to kill him afterward. The promise was made, and Henry successfully disarmed Cherokee Bill, earning him admiration and contributing to his eventual pardon.
In 1901, with the support of his family and the Cherokee Tribal Government, Henry applied for a pardon. President Theodore Roosevelt, impressed by his courage during the Cherokee Bill incident, reduced his sentence, and Henry was released from prison on January 16, 1903.
Life After Prison and a Return to Crime
After his release, Henry returned to Tulsa and worked in his mother’s restaurant. He married his second wife, Miss Ollie Griffin, in September 1903. Shortly after, their son, Theodore Roosevelt Starr, was born in 1904.
Henry attempted to lead an honest life, but officials in Arkansas sought his extradition for the 1893 Bentonville robbery. He fled to the Osage Hills and reunited with his old partners. Later, he wrote, "I preferred a quiet and unostentatious interment in a respectable cemetery rather than a life on the Arkansas convict farm."
On March 13, 1908, Henry Starr and his gang robbed the bank at Tyro, Kansas. Despite being pursued by a posse of over twenty men, they managed to escape. Henry then headed west with Kid Wilson.
In May 1908, the pair robbed the local bank in Amity, Colorado, of $1,100. Soon after, they separated. Henry spent the summer and fall hiding in New Mexico and Arizona. However, a friend betrayed him, and on May 13, 1908, Starr was arrested and extradited to Colorado.
On November 24, 1908, Henry pleaded guilty to the Amity robbery and was sentenced to 7–25 years in the Canon City, Colorado Prison. During his imprisonment, he worked as a trustee, studied law in the prison library, and wrote his autobiography, "Thrilling Events, Life of Henry Starr."
Parole and Another Crime Spree
On September 24, 1913, he was paroled but violated the terms by returning to Oklahoma.
Between September 8, 1914, and January 13, 1915, fourteen bank robberies were attributed to Henry Starr. The state legislature passed the "Bank Robber Bill," which appropriated $15,000 to capture bank robbers and placed a $1,000 bounty on Starr’s head, "Dead or Alive."
On March 27, 1915, Henry and six other men robbed two banks simultaneously in Stroud, Oklahoma, a feat that proved disastrous. Henry and another outlaw were wounded and captured in the ensuing gun battle.
Final Years and Death
After recovering from his wound, Starr pleaded guilty to the Stroud Robbery on August 2, 1915. He was sentenced to 25 years and transferred to the Oklahoma State Penitentiary at McAlester, Oklahoma.
While in prison, Starr spoke against a life of crime and was paroled on March 15, 1919.
He starred in "A Debtor to the Law," a film depicting the Stroud, Oklahoma, bank robbery. He turned down an offer from Hollywood.
On February 18, 1921, Henry Starr and three companions robbed the People’s State Bank in Harrison, Arkansas. During the robbery, Henry was shot in the back. He died from his wound on February 22, 1921.
During his 32 years in crime, he claimed to have robbed more banks than the James-Younger Gang and the Doolin-Dalton Gang combined. Allegedly, he robbed 21 banks, making off with nearly $60,000.00.
It is thought that much of the loot that Henry Starr accumulated throughout his career was hidden along the Cimarron River in Stevens County, Kansas.